Virginia offers distinctly elegant and historically relevant experiences that you won’t find anywhere else. Whether you’re looking for a romantic anniversary retreat to celebrate a big milestone in your marriage or simply in need of a relaxing spa day at an upscale resort, these eight Virginia trip ideas offer the ultimate in luxury and unforgettable, once-in-a-lifetime experiences.

Virginia Beach Oceanfront Luxury

The Cavalier

Discover luxury on the shores of Virginia when you book a stay at the Cavalier in Virginia Beach.

Luxurious Lodging: Recently reopened after a multi-million dollar renovation, The Cavalier evokes memories of the Roaring 20’s, with an old-world grandeur and southern charm that is absolutely timeless. Originally opened in 1927, the historic building now houses a bourbon distillery, the only hotel in the United States to have an on-site distillery. Additionally, the hotel has three upscale restaurants, a full-service spa, beautiful saltwater pools, and a private beach club and bar. 

The Cavalier

Fine Dining & Drinks: Dine at Becca and The Hunt Room at The Cavalier, or nearby restaurants like Zoes, Salacia, Terrapin, and The Atlantic on the Pacific. For drinks, visit The Cavalier’s distillery, Tarnished Truth Distilling Company, or grab a cocktail from the Hunt Room’s bar. There are also a wide array of  breweries in the Virginia Beach area if you’re looking to sample Virginia’s impressive craft beers.

Upscale Activities: Get a real taste of Virginia’s world-class oysters during the Pleasure House Oyster Chef’s Table Tour. This oyster experience is more than waterfront; the tour puts you knee-deep in the waters of the Lynnhaven River (wearing waders, of course) as you feast on oysters pulled out of the water only a few yards away. Hosted by the owner and oyster farmer, the three-to-four hour private dining event includes a picturesque boat ride to the oyster farm and an educational lesson in Virginia’s oysters. Bring a bottle of your favorite Virginia wine to pair with the succulent oysters for an unforgettable foodie experience.

Pleasure House Oysters, Chef's Table Tour

Pleasure House Oysters Chef 's Table Tour (Virginia Beach)

Another option for outdoor luxury lovers is the kayak tours of Back Bay National Wildlife Refuge or the Atlantic Ocean offered by Surf & Adventure. The wildlife refuge tours last approximately two hours and give you a chance to see the preserved waterways around Virginia Beach, where you may spot dolphins, loggerhead sea turtles, or other aquatic wildlife native to the region during the oceanfront tours.

Visit New Earth Farm in Pungo for a tour of the 21-acre sustainable and educational working farm. After touring the farm and perusing the brand new 2,000 square-foot market, attend one of the Farm-to-Table cooking classes, where you can learn culinary techniques from local chefs using local, seasonal produce that is both wholesome and delicious.

If relaxation is on your agenda, spend some time at The Cavalier’s Oceanfront Beach Club or Sea Hill Spa, where you can book massages, body wraps, facials, couples treatments, and a wide variety of soothing spa packages.

The Cavalier Oceanfront Beach Club

Oceanfront Beach Club at The Cavalier (Virginia Beach)

Find More To Do in Virginia Beach

Discover Virginia’s Chesapeake Bay

The lesser-known waterfront region of Virginia’s River Realm is a decadent destination for travelers looking to explore the Chesapeake Bay area.  

The Tides Inn (Irvington). image courtesy of Tides Inn

Luxurious Lodging: The Tides Inn sits on Carter’s Creek, an inlet off the Chesapeake Bay in Irvington, infusing the expected Southern hospitality of Virginia with the centuries-old traditions of watermen in the region. The resort offers pet-friendly room options if you’re traveling with your pup, but the hotel’s true luxury lies in the amenities and activities offered. Guests can rent boats, kayaks, canoes, and paddleboards to explore the surrounding waterways themselves, or they can sign up for guided sunset cruises, mixology classes, oyster roasts, bike rides, jet ski rentals, and even sailing lessons. The inn has a disc golf course, tennis courts, a lavish spa on-site, and a stunning outdoor pool area where you can lounge in the summer sun.

Coastal Dining at Tides Inn

Overlook Dining at The Tides Inn (Irvington)

Fine Dining & Drinks: You’ll find lots of fresh seafood fine dining options around the Tides Inn, like ADRIFT, owned by a husband and wife team that both formerly worked in the kitchen at the Michelin-starred Inn at Little Washington restaurant, and Merroir, the original restaurant location for the Virginia oyster superstars, Rappahannock Oyster Company.

Upscale Activities: Don’t miss the Tides Inn’s Chesapeake Gold Oyster Excursion, an immersive class that begins with a short lesson on the history of Virginia’ oyster industry, the ecology of the Bay that creates such fine oysters, and the tools used to harvest them. Once you’ve received a basic education on oysters, you’ll head out on a boat with a traditional Virginia waterman for a one-hour harvesting excursion. The waterman will let you hold the oyster tongs, feel live oysters right out of the beds, and show you how to choose the best oysters for fine eating. After returning to The Tides Inn, you’ll get a lesson in shucking, preparing, and pairing your oysters with flavorful sauces and complementary wines. The Oyster Excursion takes place every Wednesday, Friday, and Saturday during the fall season.

Virginia Oyster Trail Opening Event

Virginia Oyster Excursion at The Tides Inn (Irvington)

Another option for water enthusiasts is the Premier Sailing School at The Tides Inn. Opt for the four-day course and learn how to trim the sails, steer the boat, drop anchor, dock, tie nautical knots, and read the weather, after which you’ll receive a U.S. Sailing Basic Keelboat Certificate. If you’re only staying for a few days, the inn also offers a quick three hour sailing lesson that provides a less extensive albeit hands-on experience.

Learn to Sail: Norton Sailing School

Sailing on the Rappahannock River. photo credit: Mark Atkinson, @me_atkinson

A Luxurious Outdoor Retreat

Located at the heart of the Blue Ridge Mountains on 12,000 expansive acres, Primland, Auberge Resorts Collection offers luxurious accommodations, a championship golf course, exquisite farm-to-table cuisine, a tranquil spa, and a level of outdoor adventure that is unrivaled on the east coast.

In one of the most breathtaking mountain settings of North America, the resort boasts thrilling activities for the entire family, including horseback riding, fly fishing, alfresco yoga and meditation, kayaking, hiking, sporting clays, archery, stargazing in one of the largest observatories in the Eastern U.S., RTV trail riding, and tennis. With Auberge Resorts Collection’s highly personalized service, Primland is an inspiring escape all year long.

Photo Courtesy of Primland, Auberge Resorts Collection

Luxurious Lodging: A secluded property in the mountains of Southwest Virginia, Primland, Auberge Resorts Collection sets a high bar when it comes to luxury. In addition to the refined rooms in the main building and private cottages with every amenity you’d expect from a top resort. Primland boasts treehouses perched on a bluff 3,000 feet high with views of the Kibler Valley and mountains beyond. They provide an exquisitely unique place of serenity and soul-stirring views.

Fine Dining & Drinks: Enjoy a variety of dining experiences at Primland’s restaurants – Elements, 19th Pub, and Stables Saloon. Experience elegant fine dining in the Lodge at Elements, informal eating and imbibing at the 19th Pub, or enjoy a true southern dining experience at the Stables Saloon (seasonal). Whether savoring potato and truffle gnocchi with ocean-fresh scallops at Elements, tucking into a delectable grass-fed beef burger with an ice-cold beer at 19th Pub, or relishing true southern cooking with live bluegrass music at the Stables Saloon, gastronomic inspiration beckons at Primland. Don't forget to sample the moonshine cocktails. For a more intimate dining experience, the more private Schlumberger Wine Cellar offers bespoke, curated culinary delights.

Upscale Activities: Primland has plenty to do on the grounds. Try your hand at sport shooting on the range with clays, or hunt wild game with guides including turkey, whitetail deer, or Orvis-endorsed seasonal wingshooting for pheasant, quail, and chukar. If aquatic game is more your style, Primland offers fly fishing on the remote banks of the Dan River, which has large native populations of brown, brook, and rainbow trout, as well as three ponds stocked with trout, bass, and channel catfish. 

Rose River Farms Fly Fishing

Photo Credit: Sam Dean, @sdeanphotos

More on-site activities include horseback riding and biking on over 20 miles of trails connected to the resort, an 18-hole disc golf course designed by George Sappenfield, a pioneer in the sport of disc golf, RTV trail riding, and kayak and paddleboard trips on the Dan River. Unwind at The Spa at Primland with pampering treatments like massage, body wraps, scrubs, and nail packages. In the evenings, head to the resort’s Observatory Dome for an epic deep-space stargazing experience, viewing the unusually clear night skies above the rural resort through a high-powered telescope. Nebula or Saturn’s rings, anyone?

Play a spectacular round of golf on Primland’s 18-hole Audubon-certified bentgrass greens course, carved from the natural landscape of the mountains by renowned golf course architect, Donald Steel. The course was ranked by GOLF Magazine as one of the “Top 100 Courses You Can Play”, and is a can’t-miss course for passionate golfers visiting Virginia.

The Highland Course at Primland, Photo Courtesy of Primland

Digging Deep Into The Historic Roots of Virginia’s Wine Country

With over 300 wineries, many of them winning medals in international wine competitions, the Commonwealth is quickly becoming the premiere destination for wine enthusiasts on the East Coast.

Photo Courtesy of Barboursville Vineyards

Luxurious Lodging: Keswick Hall is the epitome of luxury, featuring Marigold, the fine dining restaurant created by world-famous Chef Jean-Georges, an on-site spa, an 18-hole golf course designed by legendary golfer Pete Dye, and a horizon pool with impeccable views of the rolling landscape. This secluded Central Virginia property is only a few miles from several notable wineries, including Keswick Vineyards, Merrie Mill Farm & Vineyard, and Southwest Mountain Vineyards.

Keswick Hall

Other Luxury Lodging in Virginia Wine Country:

The Clifton

Photo Courtesy of the Clifton Inn

Among the historic inns in Virginia, The Clifton is truly unique. Originally constructed in 1799 as a classic colonial-style home for Thomas Jefferson’s daughter and husband, Martha and Thomas Mann Randolph. Nestled in the beautiful Blue Ridge Mountains just outside of Charlottesville and on the way to Jefferson’s Monticello, the Clifton exudes historic charm with much-appreciated modern touches, a Michelin-star chef, and sweeping scenic vistas.

Albemarle Estate

Photo Credit: Jack Looney

Located on Virginia’s largest vineyard in the heart of the Monticello Wine Trail, Albemarle Estate offers guests the opportunity to stay at one of the most prestigious and architecturally significant residences in history. The sprawling estate offers a lively tasting room, library bar, outdoor pool and fishing ponds, gardens and more.

Boar's Head Resort

Boar's Head Resort

Located on more than 500 acres of bucolic countryside on the outskirts of Charlottesville, Boar’s Head is in the heart of Central Virginia Wine Country. This quintessential Virginia resort offers exceptional service and world-class recreational opportunities, including squash, tennis, and several swimming pools in the Boar’s Head Sports Club, the Audubon-certified Birdwood Golf Course (re-opening spring 2020), an on-site spa, and a trail system for hiking throughout the property.

Inn at Willow Grove 

Photo Credit: Hope Scibal

The 2019 Travel + Leisure World’s Best Awards named the Inn at Willow Grove #1 in 2019 Top 10 Best Resort Hotels in The South as well as #24 in The Top 100 Hotels in the World. Located just north of Charlottesville, and minutes from James Madison’s Montpelier, the inn blends timeless elegance and charm in a beautifully restored, sunny yellow 1770s home. Dine at the on-site Forbes 4-star restaurant, spend the day unwinding at the spa in a quaint barn behind the house, and enjoy concierge butler service with every stay.

The 1804 Inn at Barboursville Vineyards 

Photo Courtesy of Barboursville Vineyards

One of Virginia's oldest vineyards, Barboursville sits on an especially scenic parcel with historic houses, ruins, and roots which produce award-winning wines year after year. Two classic Georgian villas afford bucolic and charming suites while three more cottages offer cozy and romantic lodging perfect for a getaway.

Fine Dining & Drinks: Dine at MarigoldThe Mill Room at Boar’s Head, 1799 At The Clifton, or nearby restaurants like The Alley Light, The Ivy Inn Restaurant, C&O Restaurant, Fleurie, and Palladio at Barboursville Vineyard.

Upscale Activities: The Monticello Wine Trail contains over 30 wineries, so a self-guided tour is not advised if you plan on doing tastings at several vineyards. Instead, book a private tour with Monticello Wine Tour & Coach Co. These tours last about five hours and include stops at your choice of three or four wineries in the area, giving you about an hour at each vineyard to taste, tour, and enjoy the stunning scenery of the surrounding mountains. Several popular wineries in the region include Jefferson Vineyards, Pippin Hill Farm & Vineyards (pictured below), Barboursville Vineyards, and King Family Vineyards. Veritas Vineyards offers private Horseback Vineyard Tours, or if you’re a Dave Matthews fan, stop by Blenheim Vineyards, owned by the Charlottesville-based musician. We can’t guarantee you’ll get to meet Dave, but rumor has it that he occasionally stops by the tasting room.

Pippin Hill Farm & Vineyards

For a taste of inspiring American history, travel to Thomas Jefferson’s Monticello. Start with a tour of the house, painstakingly designed and implemented by Jefferson, then take the Garden & Grounds Tour, where you can learn about Jefferson’s lifelong love of botany and gardening as you walk the restored grounds, planted to reflect Jefferson’s designs. After seeing Monticello, spend a few hours walking the grounds at the University of Virginia, the prestigious college founded and designed by Thomas Jefferson.

Photo Courtesy of the Thomas Jefferson Foundation

Get more presidential history at James Madison’s Montpelier, about 30 minutes outside of Charlottesville. Plan your trip in early November to attend the annual Montpelier Hunt Races, now in its 84th year.


James Madison's Montpelier (Orange), Photo Credit: Big Orange Frame

Still looking for a little extra luxury during your Virginia Wine Country vacation? Boar’s Head offers hot air balloon rides that give you incredible views of the gorgeous countryside in and around Charlottesville.

Hot Air-Ballooning (Charlottesville), Photo Credit: Jack Looney

Michelin 3-Star Dining in 18th Century Style

Savor the subtle flavors of Virginia at a prestigious 3-Star Michelin restaurant, located in a charming small town in the foothills of the Blue Ridge Mountains.

Image Courtesy of The Inn at Little Washington

Luxurious Lodging: One of only 42 inns or restaurants in the U.S. to be named an esteemed Relais & Chateaux property, The Inn at Little Washington is located in Washington, another charming small town of Virginia that was surveyed and founded by George Washington in 1769. All of the 23 rooms and suites at the inn provide elegant accommodations, but for over-the-top opulence, book room six, which was inspired by the plush Ritz Hotel in Paris. All stays include a welcome cocktail upon arrival, afternoon tea, house breakfast, complimentary valet parking, and a guaranteed dining reservation each evening at the inn’s restaurant, which has been awarded three Michelin stars.

Image Courtesy of The Inn at Little Washington

Other Luxury Lodging:

Fine Dining & Drinks: The obvious choice for luxury dining is The Inn at Little Washington’s Restaurant, the only 3-Star Michelin restaurant in Virginia or even the greater D.C. area. Helmed by James Beard-winning chef Patrick O’Connell, the restaurant has been rated the number 1 inn in North America and number 2 in the world in Travel + Leisure Magazine’s World’s Best Awards. Other local upscale dining options include Griffin Tavern and Foster Harris House.

Image Courtesy of The Inn at Little Washington

Upscale Activities: Traverse Skyline Drive, the winding scenic drive that runs through Shenandoah National Park. One of the park’s four entrances is only a few miles from the inn, giving you a prime access point to the route. Stop along the way to hike through some of Virginia’s most magnificent landscapes.

Hazel Mountain Overlook, Photo Credit: Samantha Brooke, @samanthabrookephoto

Spend a day wine tasting when you visit The Inn at Little Washington. The Fauquier County Wine Trail stretches north of Washington and has almost 30 wineries and cideries, including Linden Vineyards, Delaplane Cellars, Philip Carter Winery, and RdV Vineyards, an exclusive appointment-only winery where your visit entails an in-depth tour of the property and a tasting paired with locally-sourced cheese and charcuterie.

RdV Vineyards

RDV Vineyards (Delaplane), Photo Credit: Jeff Maurtizen, @jeffmauritzen

Historic Elegance in Virginia’s Colonial Capital

History comes alive during educational and hands-on tours at this famed destination.

Colonial Williamsburg

The Governor's Palace at Colonial Williamsburg, Photo Credit: Mark Atkinson, @me_atkinson

Luxurious Lodging: If you’re interested in getting a little extra luxury during a visit to Colonial Williamsburg, stay at The Williamsburg Inn, an alluring inn just steps away from the Revolutionary City. This pet-friendly establishment offers world-class dining, recreation and amenities, such as a full-service spa, tennis courts, two outdoor pools (one of which is heated), and an indoor pool at the spa, as well as complimentary shuttle service around the grounds of Colonial Williamsburg. Child care services can also be arranged by request.

The Williamsburg Inn (Colonial Williamsburg)

Other Luxury Lodging Alternatives:

Williamsburg Winery Vineyard

Fine Dining & Drinks: Dine on-site in the Rockefeller Room, or at one of the local fine dining options like Fat Canary, Le Yaca French Restaurant, or Wedmore Place’s Cafe Provençal, where you can also sample Coastal Virginia wines at The Williamsburg Winery. Indulge in the Thomas Jefferson Wine Dinner at King’s Arms Tavern, a special historic dining experience offered multiple times throughout the year.

Upscale Activities: Visit Colonial Williamsburg and wander the colonial streets just outside of the Inn. If you get tired, grab a carriage ride to explore the historic area in style. Book a Behind-The-Scenes Tour of Colonial Williamsburg for a private tour filled with little-known facts and secrets of America’s early leaders.

Golfers should fit in a round on the links of Golden Horseshoe Golf Club, which features three separate pristine courses to total 45 unique holes. The Gold Course at the club has been ranked as one of “America’s 100 Greatest Public Courses” in 2019 by Golf Digest.

The Golden Horseshoe Golf Club in Williamsburg

Golden Horseshoe Course at The Williamsburg Inn. Photo Credit: Scott K. Brown

The Equestrian Experience in Virginia’s Horse Country

Virginia's Horse Country is the true essence of luxury travel, containing everything you need for an elegant countryside retreat.

Salamander Resort: Equestrian Center

Salamander Equestrian Center (Middleburg), Image Courtesy of Salamander Middleburg 

Luxurious Lodging: Set in the foothills of the Blue Ridge Mountains in Virginia’s famed horse country, Salamander Middleburg is a countryside estate just 50 minutes west of Dulles International Airport. Book a deluxe room at the resort, or for special occasions, consider upgrading to one of their 17 lavish suites. The resort features an equestrian center with fully-equipped stables and practice ring, a pool and outdoor cafe, hiking and biking trails, archery, fishing, zip lining, tennis and basketball courts, a disc golf course, and even falconry lessons. Book treatments at the resort’s spa, an indulgent 23,000-square-foot facility that sees to your every comfort.

Image Courtesy of Salamander Resort

Other Luxury Lodging in Virginia’s Horse Country:

The Goodstone Inn

Photo Credit: Jumping Rocks Photography, @jumpingrocksphoto

Just 50 minutes west of Washington D.C., you'll feel hours away. Escape to the Goodstone Inn, a romantic country inn in the heart of Virginia's wine & hunt country offering elegant guest rooms, suites, and award-winning French inspired cuisine. 

L’Auberge Provencale Bed & Breakfast

Photo Credit: Jumping Rocks Photography, @jumpingrocksphoto

The innkeepers of L’Auberge Provencale have meticulously transformed a historic farmhouse,  likely to have been slept in by George Washington, into a quintessential French Country Inn in Virginia’s Shenandoah Valley. Enjoy the exceptional onsite dining, well-appointed rooms and suites, the faux-painted walls, the unmistakable Provence fabrics gracefully moving in the breeze, the slower pace of the South, pastoral views of the surrounding countryside.

Fine Dining & Drinks: There are many farm-to-table fine dining options in the area, including L’Auberge Provencale’s French Restaurant, the Goodstone Inn Restaurant, and Hunter’s Head Tavern. For a more hands-on dining experience, Harrimans Grill at Salamander Resort has an adjoining cooking studio that lets you learn from the resort’s chefs during interactive cooking classes that utilize seasonal ingredients.

The Conservatory Restaurant at Goodstone Inn (Middleburg)

Upscale Activities: Salamander offers an extensive list of on-site activities, so we recommend spending at least a day on the property to get the full experience. For the horse lovers, there are several equestrian programs that you can sign up for, whether you take in the pristine countryside during a trail ride, learn the basics of horseback riding during private lessons, or book a half- or full-day package that includes all of the above and more. Don’t miss meeting Cupcake, the resort’s resident celebrity (she was featured in People magazine!) miniature horse.

Salamander Spa (Middleburg), Image Courtesy of Salamander Resort

The charming town of Middleburg centers around the historic Main Street, lined with quaint boutiques and many well-established antique shops. Stop by The Red Fox Inn & Tavern for a little local history. Dating to about 1830, it is believed to be one of the oldest continuously running inns in Virginia. At The National Sporting Library & Museum, discover the rich history behind equestrian, angling, and field sports, including archery, shooting, steeplechasing, polo, and foxhunting.

While the region is widely known for its equestrian roots, the countryside is also home to several noteworthy wineries. Greenhill Winery & Vineyards, Boxwood Estate Winery, and Chrysalis Vineyards are all a short distance from Salamander Resort. In fact, Salamander hosts a Wine & Cider Bike Tour that takes you to Boxwood Estate and Mt. Defiance Cidery & Distillery, combining the beautiful scenery of Middleburg with the best of the region’s beverages.

An Iconic Stay in Virginia’s Capital City

Visit Virginia's capital city and stay at the classic Jefferson Hotel for a memorable experience.

Jefferson Hotel

The Jefferson Hotel (Richmond), Photo Credit: Jamie Hayes

Luxurious Lodging: Since 1895, Richmond’s Jefferson Hotel has been the epitome of luxury, with breathtaking architecture both inside and out. While the rooms offer plenty of amenities (think televisions built into the bathroom mirrors, Molton Brown shower products, and plush bathrobes), the real showstopper sections of the hotel are the lobby areas; the two-story Rotunda Lobby is lined with massive marble columns and adorned throughout with sumptuous furnishings, and the main entrance lobby, called the Palm Court, is illuminated by an expansive Tiffany stained-glass dome. Just off the hotel lobbies are two restaurants, a full-service salon, an indoor pool and fitness area, and even a florist.

Jefferson Hotel

The Jefferson Hotel (Richmond), Photo Courtesy of Jefferson Hotel

Fine Dining & Drinks: Enjoy an upscale dinner at The Jefferson’s Lemaire Restaurant, and on Sunday mornings, don’t miss the hotel’s Champagne Brunch, an all-you-can-eat meal complete with custom-made omelets and waffles, fresh seafood, and tables full of seasonal fare. This isn’t your average buffet, it’s a lavish feast filled with every brunch menu item you could possibly desire. Richmond has no shortage of critically-acclaimed restaurants outside the hotel, too; L’Opossum, The Roosevelt, Shagbark, and Brenner Pass are just a few of the hot spots known for their culinary masterpieces. Follow up your meal with drinks at The Jasper, Can Can Brasserie, or one of the capital city’s rooftop bars.

quirk rooftop bar

Q Rooftop Bar at Quirk Hotel (Richmond), Photo Credit: Todd Wright, @toddwrightphoto

Upscale Activities: Experience Richmond’s burgeoning food scene with a Real Richmond Food Tour. Centered around ten of the city’s biggest foodie neighborhoods, private tours can be customized to your taste and appetite.

First settled by colonists as a town in 1742, Richmond is teeming with historic sites. Visit the grand Virginia State Capitol, designed by Thomas Jefferson in 1788, and St. Johns Church, a National Historic Landmark made famous by Patrick Henry’s “Give Me Liberty or Give Me Death” speech.

Virginia State Capitol (Richmond), Photo Credit: Bill Crabtree, Jr.

Maymont, a 100-acre American estate bequeathed to the city by the affluent Dooley family, frames the history of the property within the picturesque grounds, which contain Japanese and Italian gardens, a Nature Center that showcases Richmond’s abundant wildlife, and a farm that offers VIP Animal Experiences.

Gardens at Maymont (Richmond)

Richmond also has outdoor activities in spades, including kayaking the James River, mountain biking on over 50 miles of trails, and biking or hiking along the Capital Trail, a 52-mile paved trail that connects Richmond to Williamsburg, with notable historic sites all along the way. 

These eight luxury vacation ideas are just a small sample of what Virginia has to offer; where are your favorite getaway spots to celebrate those special, splurge-worthy occasions?